Nitrogen → Methyl 2-(5-bromothiophen-2-yl)acetate

HRID 2060345

Reaktionsgleichung

Reaktionsgleichung von HRID 2060345
N#N.[CH3:3][O:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:3][O:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][C:9]([Br:13])=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 67184N-bromobutanimideHCID 88055Methyl thiophen-2-acetate

Produkt 1

HCID 12403315Methyl 2-(5-bromothiophen-2-yl)acetateAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(The following reaction is carried out in an anhydrous N2 atmosphere.) Dissolve thiophene-2-yl-acetic acid methyl ester (42) (2.0 g, 12.8 mmol) in anhydrous chloroform (9.0 mL) and glacial acetic acid (9.0 mL), add N-bromosuccinimide (2.3 g, 13.0 mmol) in portions and stir the mixture for 3 d at rt. Add water to the reaction mixture, separate layers and extract the aqu. layer with dichloromethane. Wash combined organic layer several times with a 1 M aqu. NaOH and water and once with brine and dry it with Na2SO4. Purify the crude product by preparative radial chromatography (CyH/EtOAc 5+1] to obtain (5-bromo-thiophen-2-yl)-acetic acid methyl ester (43) as a yellow oil (2.46 g, 81%) which is used without any further purification. 1H NMR (400 MHz, CDCl3): 3.71 (s, 3H); 3.75 (s, 2H); 6.67 (d, 1H, J=3.8 Hz); 6.88 (d, 1H, J=3.8 Hz).

Aufarbeitung

  1. custom(The following reaction
  2. customAdd water to the reaction mixture, separate layers
  3. extractionextract the aqu
  4. washWash
  5. dry with materialNaOH and water and once with brine and dry it with Na2SO4
  6. customPurify the crude product by preparative radial chromatography (CyH/EtOAc 5+1]

Quellen und Nachweise

ORD-Eintrag
ord-35f9a2459c0e4343ae5af26d3f52bed6
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278356B2

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